702: I Turned My Disney-Inspired Running Skirts into a Profitable Side Hustle and a $120,000 Exit

The Side Hustle Show

Nick Loper

Business, Education, Entrepreneurship, How To

4.7 • 1.6K Ratings

🗓️ 16 October 2025

⏱️ 52 minutes

🔗️ Recording | iTunes | RSS

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Summary

What if you could turn a hobby into a six-figure business, grow it while raising three kids and living overseas, and then sell it for $120,000? Samantha Hamilton did exactly that with her former Disney-inspired running skirt business, Dottie for Running. What started as a mom-made tutu she wore to races turned into a thriving e-commerce brand serving a passionate niche community. In this episode, Samantha shares how she identified the opportunity, navigated the challenges of production and growth, and ultimately prepared the business for a successful sale through Flippa. Tune in to Episode 702 of the Side Hustle Show to learn: How to turn a niche passion into a six-figure side hustle selling Disney-themed running skirts How to build brand loyalty and community through ambassadors and social media How to scale handmade products while keeping production lean and quality high Full Show Notes: Disney-Themed Running Skirts: From Hobby to a $120,000 Side Hustle New to the Show? Get your personalized money-making playlist ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠! Sponsors: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Mint Mobile⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Cut your wireless bill to $15 a month! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Indeed⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ – Start hiring NOW with a $75 sponsored job credit to upgrade your job post! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Quo (formerly OpenPhone)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Get 20% off of your first 6 months! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Shopify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Sign up for a $1 per month trial! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Policygenius⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Compare free life insurance quotes from top companies and see how much you could save. About The Side Hustle Show This is the entrepreneurship podcast you can actually apply! The award-winning small business show covers the best side hustles and ⁠⁠⁠⁠⁠⁠⁠⁠⁠side hustle ideas⁠⁠⁠⁠⁠⁠⁠⁠⁠. We share how to start a business and ⁠⁠⁠⁠⁠⁠⁠⁠⁠make money online⁠⁠⁠⁠⁠⁠⁠⁠⁠ and offline, including online business, side gigs, freelancing, marketing, sales funnels, investing, and much more. Join 100,000+ listeners and get legit business ideas and ⁠⁠⁠⁠⁠⁠⁠⁠⁠passive income⁠⁠⁠⁠⁠⁠⁠⁠⁠ strategies straight to your earbuds. No BS, just actionable tips on how to start and grow your side hustle. Hosted by Nick Loper of ⁠⁠⁠⁠⁠⁠⁠⁠⁠Side Hustle Nation⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Transcript

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0:00.0	How a handmade skirt sparked a profitable online business and eventually a $120,000 sale.
0:08.2	Along the way, my guest today got married, moved overseas, had three kids, and still managed
0:13.9	to keep growing the business before ultimately selling it for that six-figure payday.
0:19.5	Stick around in this one.
0:20.6	We're breaking down how she came up with the idea, found her first customers, and drove
0:24.4	consistent sales for a handmade product that she didn't have to be the one making.
0:29.6	Formerly of Dottyforrunning.com, Samantha Hamilton.
0:34.0	Welcome to The Side Hustle Show.
0:35.5	Thank you so much for having me.
0:37.0	It's lovely to be here.
0:38.2	You bet. So Dottie for running. This is a business to sell Disney inspired skirts into a
0:45.6	niche within a niche market, as I understand it. There's people who love to run, and then there's
0:50.7	people who love Disney. And then there's an overlap there of people who love to run and love Disney.
0:55.6	And they really love these skirts.
0:58.2	So much so that the business really blew up post-COVID, the return to these run Disney events in 2021.
1:06.2	Tell me about what was going on in the business at that point.
1:08.4	I was living in Germany at the time.
1:11.3	And all of us were having to get quite creative with our businesses and how to keep things rolling
1:16.9	throughout the shutdowns and everything. And then when Run Disney finally did reopen the race seasons,
1:23.8	and they came back in 2021 with their sort of big return to in-person races.
1:30.3	I had my first six-figure quarter in sales. And so that was a very, very big moment and a very
1:38.2	like legitimizing moment. Yeah. Wow. Yeah. And then when I personally got to go back to my first post-COVID run Disney event and see the
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